反应 #82739

反应方程式

methylene chloride ether

ethyl ether hexane

water

(-)-4-(3-cyanophenyl)-2-trifluoromethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid

→

title compound

收率 99.0%

(-)-4-(3-Cyanophenyl)-2-trifluoromethyl-4,6,7,8-tetrahydro-5 (1H)-quinolone

收率 99.0%

溶剂

N-methylpyrrolidin-2-one

反应条件

后处理

1. 1
   其他The cooled reaction mixture
2. 2
   萃取extracted twice with ethyl ether
3. 3
   洗涤The combined ether extracts were washed twice with water
4. 4
   干燥dried (MgSO4)
5. 5
   过滤filtered
6. 6
   其他the solvent removed
7. 7
   其他to yield an off-white solid

实验过程

A stirred solution of (-)-4-(3-cyanophenyl)-2-trifluoromethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid (3.93 g, 10.85 mmol) in N-methylpyrrolidin-2-one (24 mL) was placed in a preheated oil bath at 210° C. for 20 minutes. The cooled reaction mixture was then poured into water (200 mL) and extracted twice with ethyl ether. The combined ether extracts were washed twice with water, dried (MgSO4), filtered and the solvent removed to yield an off-white solid. Chromatography (eluent: methylene chloride/ether 9:1) and trituration with ethyl ether/hexane provided the title compound (3.42 g, 79%) as a white solid mp 187°-189° C. NMR: 1.88-1.91 (m,2H, CH2), 2.21-2.25 (m,2H, CH2), 2.53-2.64 (m,2H, CH2), 4.68(d,1H, J=5.3 Hz, CH), 5.61 (d,1H, J=5.3 Hz, CH), 7.50-7.54 (m,2H, Ar), 7.61-7.66 (m,2H, Ar), 9.42 (s,1H, NH); MS: m/z=319(M+1); [α]D23 =-606.8° (c=0.665 methanol). Analysis for C17H13F3N2O: Calculated: C, 64.14; H, 4.12; N, 8.80; Found: C, 64.07; H, 4.24; N, 8.78.

来源